Stories Are Entrepreneurs' Most Powerful Tool. But What Ingredient Gives Them Power?

Most of our greatest lessons are learned when life throws us a curve ball.
Stories Are Entrepreneurs' Most Powerful Tool. But What Ingredient Gives Them Power?
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Speaking Coach and Communication Consultant
15+ min read
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I was introduced to the conference not because someone forwarded me a link or because I was casually browsing YouTube videos.

It happened on a day in 2007 when I visited my father in upstate New York. He showed me a documentary made by none other than Daphne Zuniga, known to many of my generation as Princess Vespa from the Mel Brooks movie Spaceballs. Zuniga had put together an entire documentary on the TED conference that year – back when it first started getting notice on the Internet.

The documentary featured TED2006, a year that would eventually be associated with folks like and Al Gore. It also demonstrated an early exploration of a virtual keyboard and a variety of other talks as well.

But one thing stood out for me in particular when I watched.

Somewhere in the middle of the documentary I saw an excerpt of one of the conference’s talks being given by a bespectacled British man. He spoke of a young girl from the 1930’s who couldn’t sit still in class. She disrupted class because of her fidgeting, and when her mother took her to a specialist he interviewed her briefly and then escorted the mother out after turning on the radio. When they observed her through a window in the door, they saw her moving around to the music playing from the radio. The specialist declared that she wasn’t disrupting class because she was sick, but rather because she was a dancer. This young girl studied , went on to dance professionally, became a choreographer, and choreographed famous musicals such as Cats and Phantom of the Opera. Her name was Gillian Lynne.

And the bespectacled man’s name was Sir Ken Robinson.

I would go on to watch many TED talks after that day at my father’s house, and would find a deep appreciation for many of the ideas and methodologies shared on those stages. But Sir Ken’s talk, “Do schools kill ?” was the origin story of that love affair. Today, it is the most viewed talk on the TED website, and as of this writing has 68 million views. And while it’s dubious to assign causality to something as subjective as a body of content, it feels fair to say that that story about Gillian Lynne was at least part of the driving force of the talk’s ongoing popularity for a decade-and-a-half. The audience spontaneously broke out into applause when the story was over – even though the talk itself wasn’t. The story even heads the first chapter of The Element, the book Sir Ken published several years later.

Related: How to Use Storytelling to Sell Your Brand and Vision

And yet, the story was only two minutes long.

Theoretically, this quick little story is responsible for inspiring and even empowering millions. It led to two other TED talks by Sir Ken that likewise have multiple millions of views. And it certainly stayed with me as I went to a Barnes & Noble in 2009 to meet Sir Ken and buy a copy of The Element – getting there early enough to get a seat for what became standing-room-only.

But what is it that gave it that power? What was it about a story of a little girl in the 1930’s that made it land so fully and decidedly in our hearts and minds?

And is it possible that we as entrepreneurs and visionaries can harness that power in the stories we tell ourselves?

The Common Wisdom Around Stories

Ask anyone who’s ever endeavored to share their ideas with the world, and they’ll agree that stories have power. This isn’t a secret to many people anymore. I’ve been to a number of events and listened to a variety of talks all related to the power of storytelling, and the message is pretty consistent: Use stories to attract others to your stuff.

If you’re pitching an idea to investors, use a story to convey the emotional significance of your product’s impact. If you’re looking to inspire your employees, share a personal story about your struggles to help your team relate to you as their leader. And if you’re giving a talk or are writing a book, use stories to teach the concepts that will help your audience succeed.

But over the years, I’ve asked other people what they think it is that makes a story so powerful. Some say that it’s because they don’t just appeal to the audience member’s intellect, but also their feelings. Others say that it gives the audience someone to root for. And still others will speak to the scientific implications of storytelling, such as pointing out studies that correlate storytelling with the release of oxytocin in the brain.

These observations are all true. Storytelling very much does do all of these things. But these explanations also only speak to impact – they speak to what happens when we hear a story.

Impact is, of course, essential if we’re to be of influence as entrepreneurs. But plenty of people have sought to have an impact with their stories and have fallen short.

One time very early on in my career as a consultant I suggested to an aspiring author that he begin his book proposal with a story. When I read it I saw that he took my advice.

But all that happened in the story was that he and an acquaintance walked down a path together at a conference.

That was it.

And as far as I can tell, he never got a book deal.

Additionally, I’ve noticed an alarming trend among those who speak to the power of stories. On multiple occasions, I’ve watched a talk either online or in-person that speaks to the power of stories…

And yet the entire presentation is devoid of stories itself.

I remember I once saw one of those five-minute Ignite talks where they show twenty slides for fifteen seconds each. The talk was mostly on the power of storytelling, but sadly the speaker didn’t commit even ten or twenty seconds of his five minutes to actually share a story as an example.

What this trend of poor and/or non-existent storytelling shows us is that many of us embrace the common wisdom that stories can be powerful, but we struggle to actually find the stories that help us to inspire others into action.

That powerful story – the one that makes people spontaneously erupt into applause – can often elude us.

This elusive quality may very well be because people don’t tend to speak to the ingredient that gives a story its power – the ingredient that led to all of the applause that Sir Ken received that day in 2006. It’s an aspect of a true story about ourselves that has been hiding in plain sight all of this time, and is the most critical aspect for telling a story that has the impact we want it to have.

And we can uncover this elusive ingredient by hearing a story about, believe it or not, my fourth grade play.

The Flying Slipper

When I was in the fourth grade, I was cast as King Louie the orangutan in my class’s production of The Jungle Book. It was a condensed telling of the animated Disney film, which meant that my role featured the song-and-dance number “I Wanna Be Like You.”

Throughout the rehearsal process I threw myself into my number week after week – my fourth grade teacher gave me free reign and as a result I choreographed a pretty literal interpretation of the song’s lyrics. When I got to the point of the song that declared myself “the jungle VIP” I actually just spelled out those letters. I vigorously shook my head up and down when I sang “you see it’s true-oo-oo.”

It didn’t matter that I wasn’t very creative in my interpretation. None of that was as significant as the extravagant amount of energy I committed to the dance-off I did with the girl playing Mowgli after I was done with the lyrics. I threw myself all over the stage. I kicked my legs every which way. What I lacked in nuance I more than made up for with zeal.

But then we got to opening day. We were to perform in front of about half of the elementary school, and it was the first time we wore all of our costumes. I wore an oversized brown shirt stuffed with newspaper, a wig, a mask with a big hole to show my face, brown tights, and furry gorilla slippers. I began my number with my lame choreography and the audience began laughing right away. But when we got to the dance-off I started kicking my legs every which way as I always had.

And then my left gorilla slipper fell off my foot.

It landed unceremoniously on the floor between the stage and the audience, and I had the fourth-grade equivalent of an “oh crap” moment.

But a split-second later, I simply reared back my right foot and hurled the other slipper off as hard as I could. It sailed halfway back across the auditorium.

Everyone went berserk.

The response to the flying slipper was so positive that I deliberately kicked my slippers off for every performance thereafter. When the first graders and kindergarteners sent us cards made out of construction paper, a number of them wrote about how much they liked it when “the lion” kicked off his slippers.

I realized that sometimes the greatest catastrophes are the greatest opportunities for success.

Now, I’d like you to consider something. You may have noticed that, just in that last paragraph break, I offered a lesson at the end in the form of a realization I had in response to what happened. This is similar to the trend in Aesop’s Fables, when he explicitly states a lesson at the end. For example, in the story of the Tortoise and the Hare, the final sentence is the lesson “slow and steady wins the race.”

The lesson in a story is of particularly significant value when someone is sharing it as way to influence others, for it becomes the primary takeaway for the audience. The lesson is what those who listen to a pitch will glean as the wisdom behind a product or service, and it’s the basis of the actions one is supposed to take when they read a prescriptive article or book.

Related: 3 Ways to Tell Your 'Brand Story' So Your Audience Won't Tune You ...

It’s also of significant value in the context of a TED talk or another type of presentation, for the essential lesson becomes what the TED community calls the “idea worth spreading.”

For example, in the case of Sir Ken’s story about Gillian Lynne, he lays out how that experience at the specialist’s office was critical to her creativity and the potential she eventually realized in her life. Shortly after he conveys the idea that our only hope for the future is to see our creative capacities for the richness they are.

But how does a story prompt this lesson and ensure its intrinsic value to others? What is it that ensures we get this gift from all of that oxytocin spreading through our brains?

The Source of a Story’s Power

As we just established, the takeaway from my Jungle Book story was the lesson that sometimes the greatest catastrophes are the greatest opportunities for success. It’s a clear prescription for how to succeed in some aspect of life, much like I outline in this article on elevator pitches.

But what aspect of the story prompts that lesson? What is it about the story that leads to this insight?

To answer this question, I’d like you to consider what might happen if I were to tell you a different story. What if I told you that on that opening day, I went on stage and sang and danced just like I had at every rehearsal? What if I finished my number and everyone applauded and I went on with my day?

Your first reaction would probably be, “that’s a really boring story.” And you’d be correct. It would be as anticlimactic as the story from that book proposal where the two men walked along a path at a conference.

But perhaps even more significant than its lack of entertainment value would be the fact that there’s no lesson to be gleaned from it. I rehearsed for a performance and the performance went off without a hitch. So what? Theater companies have been doing that since the ancient Greeks put on plays by Aeschylus and Euripides.

I had the insight I had because the slipper fell off. It was a lesson about catastrophe, and I learned something when I responded to that catastrophe.

Because the slipper fell off, I was forced to adapt to a new way of doing things. And in that adaptation – that shift into a different way of being – I learned what I did.

This means that the main ingredient in a true story about our lives is an event we didn’t see coming – an unexpected moment.

In this way, the value of a true story about our life is determined by the extent to which it incorporates the unexpected.

The Unexpected Shows Up in Every Story Worth Telling

Let’s look at this idea through the lens of the stories we’ve already explored in this article. Remember when the specialist told Gillian Lynne’s mother that she wasn’t sick but rather was a dancer? Up until that point in the story, the common belief was that she was disruptive because she was somehow compromised in her health or capacity – that she was hopeless. But the specialist surprises Ms. Lynne as well as us with the revelation that her restlessness was being caused by something else entirely.

When my father showed me the TED documentary, I enjoyed the first half of it with interest and appreciation. But when Sir Ken told his story, I was suddenly transfixed. I was suddenly consumed with what I was seeing. That sudden shift was a moment of the unexpected.

And there are a whole variety of other stories that feature the unexpected, such as when Elizabeth Gilbert shares the story of her time at an ashram in India in her phenomenally successful book Eat, Pray, Love. She decides that she’s been too chatty with others and needs to be more like some of the ashram’s most austere residents – silent and solemn. Right after she decides this, she’s given the job of being a hostess to other residents – thus making silence basically impossible.

On day 21 of his famous 30-day experiment immortalized in the documentary Super Size Me, filmmaker Morgan Spurlock has heart palpitations. He’s forced to consider daunting advice from his doctor to end the experiment.

And, when TED speaker Susan Cain gave her talk on introverts, she began with the story of when she goes to summer camp with the impression that she’s going to be in a cabin full of girls reading all summer. She finds out that the opposite is true.

Each time the person in the story encounters something they didn’t see coming, they’re forced to adapt. Ms. Gilbert must rethink what it means to commit herself to spiritual growth. Mr. Spurlock must consider what he values most. Ms. Cain must set a new context for her time at camp as well as her beliefs about her own life as an introvert.

Something happens that they didn’t see coming, and they must adapt. This is when they learn.

Our Opportunity in 2020

That day at my father’s house came to be one of the more significant ones of my own career, given how much I’ve utilized best practices from the TED stage to teach others in the years since.

As a result of being unexpectedly transfixed by Sir Ken’s story, I would benefit from many other TED talks in the years to come.

This was particularly valuable when it came to helping speakers and authors with their content, but there was something else that happened many years earlier that was even more formative.

When I was 18, I went with my family to a party being thrown by one of my parents’ friends. Though during my earlier teenage years I was rather withdrawn around adults, on this night I felt like I had come out of my shell and spoken to a number of people. This pleased me. When we got home that night, my father made an observation to me.

“Whenever I heard you in a conversation,” he said, “you were doing all of the talking.”

When my father said this, he didn’t have any judgment in his voice. He didn’t say anything that shamed me. He just made the observation.

He may not have shamed me, but I did indeed feel shame – so much so that for years I observed and amended my interactions with others, as well as how I crafted content. Eventually I came to see it as a victory if my curiosity about the other person’s world drove the entire conversation – if after an hour of speaking they hadn’t learned anything about me.

That unexpected comment from my dad was the origin story of the larger insight that drives my own philosophy: that effective communication values the recipient over the sender.

It was a Wednesday in November of last year that I realized that conversation with my dad was the beginning of my life’s work. That night, I shared that story and its accompanying revelation with my dad as he lay in a hospital bed.

He died four days later on the following Sunday.

Though he had been ill for several months, I would be lying if I said I had expected his passing to come so soon. He had overcome many different illnesses over the years. But because of a medical error, he succumbed and I was left with a greater need to adapt than I ever had been before.

Sir Ken Robinson, that giant of storytelling, passed away recently as well. It is one of many losses we’ve faced in 2020, including the loss of our lifestyle, our thriving economy, and over a million of our brothers and sisters around the world to a global pandemic.

In this way 2020 has become synonymous with disruption – a series of events that we simply didn’t see coming. It has caused a multitude of issues, and arguably has shifted the baseline of what will be necessary to maintain civility and loving kindness.

But Sir Ken’s passing also reminds us that the stories we share may not just be a powerful way to influence those who most need our help; they very well be most important element of our legacy.

One of the clichéd terms I’ve heard most since March is that we live in “uncertain times.” But the truth is that we always have. Life is full of uncertain outcomes. Each day is its own beast to slay.

And what the unexpected grief of losing my dad taught me, at the end of 2019, is that the many losses we're facing now will leave us with opportunities.

I encourage you to look at the unexpected nature of this year as ground zero for some of the most powerful stories we ever may tell. Mine the moments from your life that you didn’t see coming. Share them with someone who will benefit from your insights.

Yes, doing so will help you to attract new followers, get funding, or even help your content to go viral.

But they will also help you to share your life with someone who won’t be here forever.

Related: Storytelling Can Help Anyone Connect to Your Brand

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